Aaron Zander: Tip of the spear for employee success teams

An interview Zander, Head of IT at HackerOne.

What do you ACTUALLY do?

I think the goal in modern IT is to be the tip of the spear for “employee success” teams — HR, Facilities, IT, Security. At the end of the day all these teams need to use tools that IT controls, and our goal is to make sure that every employee has the tools they need to be successful and secure without creating a million steps just to login.

What types of devices do you support?

macOS and ChromeOS only. We’re about 80/20 right now macOS to ChromeOS devices.

What’s your favorite piece of tech?

Lately? Beyond corp tools like Duo Beyond, ScaleFT, etc., I love tools that allow users to be more secure with easier processes than a VPN. Tools that encourage users to update their own devices rather than forcing them down on the user without choice. Though they are similar, the feeling is different.

What tools or apps are most important to your job?

Slack, G Suite, Okta. Maybe not in that order, but without those tools nothing here would happen.

Do you prefer hands-on, or troubleshooting from afar?

I don’t think it’s an either-or situation. Sometimes all that can be done is remote troubleshooting. We are about 30% distributed, up until recently, 30% of the “in office” folks relied on just me in California, despite the fact that we have offices in Groningen, New York, and London. Good remote support makes you better at in-person support. It makes you better at training and explaining your solutions to your users. Try this: Grab a teammate, grab a laptop that’s factory defaulted. Turn back to back and have one person guide the other into just installing Google Chrome. It’s harder than you think, especially if the other person “plays dumb”.

Favorite thing about your IT environment?

The automation of it all. A few years ago at a different organization I wrote this: Bringing Okta to Massdrop. Now I do the same but with stronger security, better automation and more reach.

Thing you’d most like to change about it?

Better, easier to stand up, centralized logging.

What’s on your desk?

Beyer Dynamic headphones with an Aune dac/amp. Wireless charger for my phone, 27” dell display, Macbook Pro 13” w/ touchbar on a stand. Custom Clueboard Keyboard, various emotional support toys including a pair of ghostbusters domo kun,  a Damper Baby brought back to be from Taipei 101, a stack of computers for repairs, a whole bunch of other random swag like HackerOne challenge coins and other accumulated bits and bobs.

How did you start your career in IT?

I’d help around my mom’s office when I was a youth. That lead to running digital labs in college, running our new student orientation for computers, and teaching Final Cut Pro and Adobe After Effects. From there I ran a small freelance business helping companies build small studios and post production houses. It just kept escalating from there. Eventually I found myself at HackerOne looking at a job that, for the first time in a long time, pushed rapidly forward with the latest security tools, believed in employee enablement, was hyper-focused on transparency and honesty, and most of all had a mission I wanted to be a part of.  

What are the biggest misconceptions of your role, internally or externally?

Nick Burns, or the IT crowd. Don’t get me wrong those guys exist, and I hope they all go work in a datacenter somewhere and stop hurting the image that so many of us have spent decades repairing. We bust our butts to be the trusted point of communication, but the “no” guys make shadow IT so much more prevalent. So many of us spend a great deal of time setting up our employees for success, building their mental toolkits so they can handle all of the security intrusions coming at them from all directions. We want to provide the tools that make their lives easier and more secure at the same time.

What was your proudest professional moment?

Speaking at Oktane 2016 and being named their “Pioneer of the Year” was pretty great. Also turning around a new 19,000 sq ft office in 50 days solo from lease signing to move in made me feel pretty heroic.

What are the biggest challenges in your work?

Battling shadow IT, and education to understand how our tools work to solve the problems people frequently ask.

Most cringeworthy request?

Yeesh, this is a hard one, so many things we laugh at behind the scenes are just simple misunderstandings. I think one of the funniest ones was an employee who had been asking for a new laptop for more than a year before his manager approved. Finally the afternoon I gave it to him, his deskmate spilled an entire pint of beer on it. Not a little bit. Not a puddle near it. The entire glass, face down on the keyboard. He was crushed, certain I wouldn’t replace it. But the next morning I had another shiny new laptop for him, and we got his deskmate a few sippy cups for good measure.

Do you stay hydrated at work?

I try, start the day with a Soylent, move on to Kombucha and La Croix (because it’s San Francisco).


Depends, GUI a lot, CLI sometimes.

DIY or turnkey?

Turnkey if it doesn’t require an MSP or a $20k post sales engagement.

Where can people follow you online?

I don’t post enough anywhere to be interesting. If you like pictures of SF and my dogs then @zndr on Instagram and linkedin.com/in/aaronzander

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